


Try Harder

by mahons_ondine



Category: Check Please! (Webcomic)
Genre: Crack, I'm Sorry, M/M, Sexting
Language: English
Status: In-Progress
Published: 2016-03-01
Updated: 2016-03-19
Packaged: 2018-05-24 02:57:59
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 1,929
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/6138970
Author URL: https://archiveofourown.org/users/mahons_ondine/pseuds/mahons_ondine
Summary: <blockquote class="userstuff">
              <p>In which Jack is terrible at sexting.</p><p>Now with part two--in which Shitty is an excellent teacher, but Jack Zimmerman might be too difficult even for him.</p><p>And part three--in which Lardo used to be a phone sex operator.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> I don't know what has gotten into me. I'm so sorry! (I'm really not, although maybe a little for Bitty's texting style.)

"I miss you, Bittle." 

 

_"Awww I <3 you!!!!!!"_

 

"Are you having trouble with math homework? Ask Ransom for help, I am hopeless with numbers." 

 

_"Lol oh you"_

 

"What?"

 

_"4get it. only two more weeks!!!!!!!!!!"_

 

"I'd like to kiss you again if you're amenable." 

 

_"Yes!!? Obvi! What else?"_

 

"I would like to kiss your neck." 

 

 _"Mmm ;-) tell me more_ " 

 

"Ok. I would also like to kiss your ears. And I would like to bite on your earlobes, please." 

 

_"Lol anything else?"_

 

"Do you not enjoy that? I don't have to do that." 

_"Oh, Jack! What am I gonna do with u?"_

 

"Umm..." 

 

_"I meant like, what sexy things?"_

 

"Oh! I could take off your shirt." 

 

_"Mm and urs 2!!!"_

 

"Right. Of course. We could take off our shirts and lay down on the bed. And I could touch you?" 

 

_"Yesss. Where?"_

 

"In your room I guess?" 

 

_"Oh Jack! I meant where are u going to touch me?!!?"_

 

"On your body?" 

 

_"Yes..."_

 

"Your skin?" 

 

_"*sigh* Jack Laurent Zimmerman ur terrible at this! :P"_

 

"No, no! I promise I'm really good. Give me a chance. I really do want to have intercourse with you.  Please, Bittle." 

 

_"Lol I meant the sexting. I totally want to sleep with u 2."_

 

"Hey! I'm really good at texting! Shitty showed me how to do the smile things and everything, see: :)!" 

 

_"Oh you sweet summer child! I meant sexting- like saying sexy things by text so u can turn on ur partner!"_

 

"Why? Why would you do that?"

 

_"OMG!? Lol want me 2 show u?"_

 

"Sure." 

 

_"Alright. Alright.  So I guess I’ll tell u what im doing now”_

 

“Okay.  What are you doing?”

 

_“Well I’m naked”_

 

“Are you going to take a shower? We can just talk later if you like.”

 

_“No, guhhh!!!ljasdlfjas”_

 

“Sorry?”

 

_“it’s ok.  But no, I’m not going to shower.  I’m in bed”_

 

“Do you sleep naked?”

 

_“.. No.  I’m not sleeping, I’m touching myself.”_

“Oh.” 

 

_“I’m lying in bed naked, and I have my hand wrapped around my cock, and I’m so hard”_

 

“You do?”

 

_“Yes.  And I’m stroking myself and playing with my nipples and rocking up into my hand”_

_“And I’m imagining it’s your mouth.  I’m imagining how good my cock would look between your lips. and I’m thinking about you sucking hard on my cock, and it makes me so hard it almost hurts”_

 

“… Oh.” 

 

_“And I’m imagining thrusting in2 ur mouth, and ur tongue feels so good on my cock that I cum in ur mouth, and that thought makes me cum so hard.  Im gasping and moaning ur name and cumming all over my stomach”_

 

“oh wow” 

 

“ _Omg, I broke him!”_

 

“No, no.  I get it now.  I liked it!” 

 

_“good”_

 

“But Bitty, can I ask you something?” 

 

_“yes?”_

 

“Next time can I listen on the telephone?”

 

 

 


	2. A Little Help From My Friend

**Summary for the Chapter:**

> So this is apparently going to be a sort of disjointed little series.   
> So to the handful of you who subscribed to this, even though it was one chapter long. Congrats. You win. This is dedicated to you crazy prescient people. I had to write more.

**Notes for the Chapter:**

> I am not sorry. Not at all.   
> Where do I go next with this???

“Shitty.”

_“Yeah, brah?”_

“I need help.” 

_“Well, Jackeroo.  You’ve come to the right person.  I’m always happy to help a bro in need. “_

_“What do you need, exactly?”_

“Bitty thinks I’m no good at the sex writing thing.”

_“You’re writing erotica for Bitty?  Excellent! Written pornography has been making a comeback in recent years. We talked about it in my Sex and the modern woman class. “_

“No, no.”

_“No, we totally did.  I wrote an erotic novel about high school students exploring their sexuality and the meaning of consent. It was very well received.”_

“No, Shitty.  Not like that.  Or maybe like that?  I don’t know.”

_“Alright, alright, chillax bro.  Tell Shitty what happened.”_

“D’accord.  Ok.  So we were texting.  And he kept asking me how I would kiss him, and touch him.  And I guess I wasn’t really answering the questions he wanted?”

_“Ahhh!  You need help with sexting.”_

“Yes! That’s it, Shitty.  Sex-texting.”

_“Close enough.”_

“No! We aren’t.  It’s terrible.  He’s in Madison, and I’m in Providence, and we’re never close.  So I need to do this for him.  I want to make Bitty happy.” 

_“Jack, it’s never a good idea to change yourself to please your partner.  You should only do what you want to do.  Consent is really very important, you know.  Maybe you should read my novel.”_

“No, I do want to.  I do, Shitty.  I’m just no good at it.” 

_“Well, I have it on good authority that our Little Bits is crazy for you already, but I’d be happy to help.”_

“Great. Thank you Shitty.” 

_“Alright.  So, why don’t we start from the beginning. You pretend I’m Bitty, and I’ll help you map out your path on the way to sexting glory.”_

“Right.  Ok.  So, I said I wanted to kiss him, first.”

_“Pretend I’m Bitty.  Tell me you want to kiss me.”_

“I want to kiss you.” 

_“Ok, that’s an excellent impulse, Jack, but go a little deeper.”_

“Um, I want to kiss you while using my tongue so that I can feel deeper inside your mouth.” 

_“Ok, so more details.  Less explanation.”_

“I want to kiss you on the mouth, and use my tongue” 

_“Better, Zimms! That’s enough for now.  Let’s move on.  What else?”_

“Well he seemed to want me to talk about taking our clothes off?” 

_“Smart boy, our Bitty.  Clothes are the devil’s work.”_

“Ugh, you would think so.” 

_“I know so.  Now, I would just slip right out of my clothes, but Bitty probably would enjoy more of a show.”_

“Like a strip... striper?” 

 _“Well, how do you take your clothes off with a partner?”_  

“Slowly, I guess?”

_“There you go! Alright, Zimms.  Try it out on me.”_

“After I kiss you with my tongue, I want to take off my shirt slowly.  Then take off my pants slowly.  Then take off my boxers _very_ slowly.”

_“Ok, let’s try something.  Get up and take off your shirt, and think about all the little things you do.  Where you put your hands, whether or not they’re touching those luscious man muscles of yours? Does your flow get wrecked when you pull your shirt over your head?”_

“Ok. I did it.” 

_“Try it again?”_

“I gripped the back of my shirt with my left hand.  I held the fabric between my index finger and thumb, and I pulled it up over my head.  I stuck my right arm up in the air, and I bent it over and grasped further down the shirt, and pulled it all the way over my head.  Then I shook the shirt off my arms.  I didn’t touch my muscles.” 

_“I think you need a specialist, my man.  I may be an excellent erotic novelist, but you need more remedial training than I can provide. “_

“You won’t help me, Shitty?” 

_“Oh I’ll help you.  I just need backup.”_

“Alright.  If you say so. Just not Ransom and Holster.  They always get too wrapped up in finishing each other’s sentences to be much help. “ 

_“Your wish is my command, bro.”_

“Thank you, Shitty.”

_“No prob.  I’m going to send you my novel.  I want you to read it for homework.”_

“Will that help?”

_“Absolutely, Jack.  I’m sending it now.  It’s called ‘Omg Yes, Please! Means yes’”_

 

**Notes for the Chapter:**

> Who does Shitty go to for help? 
> 
> Will Jack ever learn to sext?
> 
> Will Jack ever be able to jack off enough to get rid of his permanent sex-writing-text-thing induced hard-on? 
> 
> I need your help guys. Guide me to a satisfactory conclusion. 
> 
> Yes. I absolutely meant that in a dirty way. 
> 
> Will Kent show up? Will there be brojobs? I have way too many ideas.


	3. Chapter 3

**Summary for the Chapter:**

> In which Jack gets double-teamed--or Lardo used to be a phone sex operator, and Jack is no closer to solving his problem.

**Notes for the Chapter:**

> First, I should say that I mention a number of fantasies that are outside of the norm in this. I don't intend any insult, and these are far, far from the strangest things I've heard. Nothing wrong with odd fantasies! Go out and make strange porn, it's the best! 
> 
> Second, this chapter is dedicated to the_boring_teacher who suggested Lardo might have been a phone sex operator. 
> 
> And finally, with three people the conversation can get confusing, but for your reference, Jack is in normal text, Lardo is italicized, and Shitty is bolded. 
> 
> Enjoy! And tell me what you'd like to see next! If I think I can manage it I will!

"Hey, Shitty. I finished your book." 

 

**"What did you think, bro?"**

 

"Well, I'm not really into girls, so that was kind of weird."

 

**"Don't let Lardo hear you say that!"**

_"It's alright! Girls can be totally weird, Jack! Weird is not a pejorative, Shitty."_

"Oh. Is Lardo with you? I don't mean to intrude. I--" 

 

**"Don't worry about it, bro. Lardo is chill, and she’s right, of course.  Nothing wrong with weird.  Maybe she can help with your problem."**

_"Right, tell Lardo of your troubles."_

"Ugh, fine. You sound just like Shitty. So, Bitty thinks I'm bad at sexting and Shitty gave me his book to try and help me. But I'm not sure I understand what to do." 

 

_"Explain."_

"Alright, so I get that consent is important--" 

 

**"Consent is very sexy!"**

"Yeah Shits, I get it. But I'm not sure how to translate it to sexting. So should I ask him if I can sext him first? Or should I ask with each sext? Or wait! I know, should I describe asking for consent?"

 

_" . . ."_

**". . ."**

 

"Ok. I mean should I say 'I lean in close and ask if I can kiss you. You respond in the affirmative, so I press my lips against yours. Then I pull back and ask if I can use my tongue when I kiss you, and you respond by saying yes, so I french kiss you. And then I ask if it's ok for me to take my shirt off, and you--" 

_"Wait. Hold up, bro. Did Shitty make you read ‘OMG Yes Please! Means yes’?"_

**"Of course I did. It's brilliant. My professor said it was a striking commentary on rape culture, and the need for more conversation in the bedroom."**

****

_"It's not helpful for sexting, though. Look, Jack, all that is great in person, but it makes your sexts very stilted. When I was a phone sex operator--"_

"Eh, quoi?" 

 

**"Oh my gosh, bro. That's so hot--helping people achieve their pleasure through safe and consensual means. Sex work can be a liberating experience for people who actually choose to do it. Wait, you weren't coerced, right?"**

 

_"Naw, it was fun."_

**"Thank you for trusting me with this."**

_"No problem, Shits."_

"Guys? Can we-- Should I call back later?" 

 

_"No, no, Shitty is giving me puppy eyes, but he will just have to wait for his chance to properly worship me until after we finish our discussion."_

 

**"Alright, bro. I'll go warm up my tongue. I leave you in Lardo's tiny, but capable hands."**

_"I'll show you tiny! Just you wait, Mr. Knight! I may be small, but these hands can pack a wallop!"_

 

". . . Uh Lardo?"

_"Right-o, Jacky boy. So here is what you need to know. Phone or cybersex is different from having sex in person. You only have your words to arouse someone, and the most important thing you can do is try to elucidate their deepest and darkest fantasies. Of course you can give someone head via sext, but think how much easier and more successful it will be for you to figure out their secret triggers. You want them to come back for more because you are the only one who truly understands them.  "_

 

"So, should I guess? Maybe Bitty has very sensitive ... Knee caps or something?" 

_"No, no, not like that. How about— Do you think he has dinosaur fantasies?"_

 

"Probably not?"

 

_"Shame. I have a lot of experience with those. How about giantess fantasies?"_

 

"Well, he is gay..." 

 

_"Right, but still you might try it. Or perhaps alien abduction? That's a classic."_

 

"I don't think so? I mean I mostly thought I would talk about kissing and touching—"

_"Hmm, no good.  Alright, how about panty sniffing? No, no--tentacle rape? Or perhaps you should try cannibalism. I had this one guy who wanted to spitroast me. Like, over an actual fire. Bitty likes cooking!"_

 

"Uh, mostly baking?"

 

_"Baking! Of course! Maybe a Hansel and Gretel fantasy?"_

 

"I think-- I think I should--Yeah, I need to go, Lardo." 

 

_"Alright, did you get what you needed? Do you think you can do it now?"_

"Eh, oui? Yes. Yes, of course Lardo. Thank you for your help." 

 

**"You leaving us, Jackeroo?"**

****

_"Are you wearing my Georgia O'Keefe shirt again, Shitty?"_

 

**"It makes me feel pretty."**

 

"Uh, right. Yeah. I'll talk to later, guys." 

 

**"Later, bro."**

 

_"Come over here--oh good you're just wearing the shirt. You can start on my toes."_

**"Yes, ma'am--ouch! Bro! I mean bro--"**

**Author's Note:**

> Bitty could use a few sexting lessons, too, actually. I bet Kent is a beast at sexting. He should hold a class.


End file.
